Methanol → Methyl thiophen-2-acetate

HRID 523134

Reaction equation

HRID 523134 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([OH:9])=[O:8].OS(O)(=O)=O.[CH3:15]O>>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([O:9][CH3:15])=[O:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 159702-Thiopheneacetic acid

Product 1

HCID 88055Methyl thiophen-2-acetateYield 91%

Procedure

Thiophene acetic acid (27.3 g, 192 mmol) was treated with a solution of H2SO4 (5.76 mL, 108 mmol) in MeOH (384 mL) at reflux for one hour. The reaction was then cooled to room temperature, concentrated by rotovap, diluted with ether, washed with 5% sodium bicarbonate and brine. The organic phase was then dried with magnesium sulfate and concentrated by rotovap to yield the product as a yellow oil (27.4 g, 176 mmol, 91%), which was used without further purification. The product matches data for commercially available methyl 2-(thiophen-2-yl)acetate (CAS No. 19432-68-9).

Workup

  1. temperatureat reflux for one hour
  2. concentrationconcentrated by rotovap
  3. additiondiluted with ether
  4. washwashed with 5% sodium bicarbonate and brine
  5. dry with materialThe organic phase was then dried with magnesium sulfate
  6. concentrationconcentrated by rotovap

Sources & evidence

ORD record
ord-a124dfd8d8a5438aaaece588359dfdb7
Source dataset
uspto-grants-2016_05
Patent number
US09334304B2

Linked notes

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